Resinate



Patented July 16, 1946 RESINATE Harold M. Spurlin, Marshallton, Del.,assignor to Hercules Powder Company, Wilmington, Del., a corporation ofDelaware No Drawing. Application August 16, 1943,

Serial No. 498,877

Claims. (Cl. 260100) This invention relates to a new composition ofmatter and the method for its production. More particularly, it isconcerned with a new resin compound and with a method for itsproduction.

In accordance with this invention it has been found that aluminumdialkoxide monoresinates may be prepared, free of excess resin acids andimpurities, by reacting aluminum trialkoxide with rosin in theproportion of 1 mol of aluminum trialkoxide to 1 mol of rosin. Themethod of this invention thus comprises reacting aluminum trialkoxidewith rosin in the proportion of 1 mol of aluminum trialkoxide to 1 molof rosin. I 'he reaction may be carried out in the presence or absenceof an anhydrous solventwhich does not react with the product. Ifdesired, the aluminum dialkoxide monoresinate may be used in solution,or the alcohol set free may be distilled 01!.

Having thus indicated the general nature and purpose of the invention,the following examples are given to illustrate the preparation of thenew resin compound and are not to be construed as limiting the same.

indicated.

Example 1 302 parts of rosin crystals and 204 parts of redistilledaluminum triisopropoxide and 800 parts of Varsol (a straight-runpetroleum fraction; boiling between 300-400 F.) were mixed and heated to150 C. to distill off 60 parts of isopropyl alcohol. Theproduct was asolution of aluminum diisopropoxide monoresinate.

no precipitation as it would if the diresinate had been present.

Example 2 29 parts of rosin crystals were dissolved in parts of drybutanol containing 20 parts of aluminum triisopropoxide. A homogeneoussolution resulted. The addition of 15 parts of butanol caused thesolution to become milky due to the precipitation of the monoresinate.The mono alkoxide diresinate is quitesoluble in butanol.

Example 3 I 2.3 parts of granular'aluminum were dissolved in- 810 partsof anhydrous butanol at'the re- 3 The addition of 3700 parts of dryisopropyl alcohol caused In the examples, the term "parts representsweight units unless otherwise (10.8% theory). The product was insolublein cold and boiling acetone, alcohol, carbltol, and

methyl celloso-lve acetate, but was soluble in a high boiling petroleumfraction (boiling point about 163 C.) at temperatures above 155" C. andin boiling tetralin.

Example 4 i 2.3 parts of granular aluminum were dissolved in 810 partsof anhydrous butanol at the refluxing temperature, and then 28.7 partsof I Wood rosin (acid number 162) in anhydrous butanol solution wereadded hot to .the hot aluminum tributoxide solution. Immediateprecipitation of thealuminum dibutoxide'monoresinate occurred. Theprecipitate was filtered off and dried under vacuum at C. 37.8 parts ofaluminum dibutoxide monoresinate were obtained. The filtrate, onevaporation to dryness, yielded 3.3 parts of residue which contained theneutral bodies in the rosin. The ash content of the product was 11.03%(10.8% theory). It had the same characteristics as the product inExample 3.

.As shown in the examples, the aluminum" dialkoxide monoresinate isprepared by reacting aluminum trialkoxide and rosin in the proportion of1 mol of aluminum trialkoxide to 1*mol of rosin, either with or withoutdistilling oil the alcohol set free. The aluminum trialkoxide 'may beprepared as illustrated in Examples 3 and 4,

' if so desired. While aluminum triisopropoxide and aluminum tributoxidehave been used as the aluminum trialkoxides, other trialkoxides ofaluminum, such as methoxide, ethoxide, propoxide,

etc., may be used. However, it is preferable to use the triisopropoxideor tributoxide, since aluminum trlisopropoxide and tributoxide are morereadily prepared, the triisopropoxide being the lower boiling and,therefore, the more readily 5 purified, and the methoxide and ethoxideare and, thereabsence of an anhydrous solvent which does not react withthe product. Hence, in place of Varsol and butanol shown in Example 1,other suitable solvents, such as a high boiling petroleum fraction(boiling point about'163 C.) at a temperature above C., boilingtetralin, xylene, may be used. Lower boiling solvents may be used, butit is then more difiicult to remove the ale cohol set free in thereaction by"-distillation. In the case of oleoresin, the solvent may bethe turpentine of the oleoresin. If it is desired tormake use of asolution of aluminum dialkoxide monoresinate, a suitable solvent wouldbe, for'example, toluene, hxana-isoprop'yl ether, carbontetrachloride.It is also advantageousto carry out the reaction in the presence of asolvent that can also be used as the solvent for the product.

or not as may be desired.

Any of the solvents for the product may be used, and the aloohol setfree in the reaction removed Since the alkoxide group of the aluminumdialkoxide monoresinate is readily hydrolyzed by water, anhydrousconditions must be used inpreparation of the monoresinate and drysolvents must be used.

The term rosin as defined herein and in the claims, and which may beused in the reparapropoxide monoresinate which comprises reacttion ofthe aluminum dialkoxide monoresinates,

includes any Wood or gum rosin; rosin crystals, oleoresin, rosin acidsobtainable therefrom, such as abietic acid, pimaric acid, sapinic acid,et'c.,1as

well as mixtures thereof. In addition, it includes the modified rosins,such as hydrogenated rosin, heat-treated :rosin, polymerized rosin, and

ing aluminum triisopropoxide and rosin crystals inetheproportion of 1.mol of aluminum triiso- 'propox-ide toil mol of-.rosin crystalsin thepresence of an anhydrous solvent. 7. The method of producing aluminumdiisoing aluminum triisopropoxide and rosin crystals .in the proportionof 1 mol of aluminum triisoence of an anhydrous solvent, distilling offthe alcohol set free, and recovering aluminum diisotpropoxidemonoresinate from the solution.

trialkoxide to 1 mol of rosin, and, if desired, the

alcohol set .free may-be distilled ofi. The reaction may be carried outin the presence or absence :of .an anhydrous'solvent. If the alcohol hasbeen driven ofi, butanol, acetone, or ethanol may be added to theresidue and aluminum dialkoxide monoresinate will .be precipitated as aresin; The product can be easily recovered by filtration. Any othersuitable method of rec'overing, the aluminum dialkoxide monoresinate maybeused'. i e

If :a solution of aluminum dialkoxide monoresinate-is desired, therosinsandlaluminum trialkoxide may be dissolved, for example,-- in ahydrocarbon solvent, and a clear solution of aluminum dialkoxidemonoresinate results. 2

- .There is thus'provided by the'invention a new composition of matter,aluminum dialkoxide monoresinate, free of excess acid and 'impuri ties,and a method for preparing it. The mono" resinate .is a definitecompound which is relatively insoluble in cold and boiling acetonaalcohol; carbitol, and methyl cellosolve acetate. Furthermore, it"isinsoluble in 'butanol in contrast with the alkoxide diresinate andtriresinate, both of'wl'iich are quite soluble in this alcohol. It hoevensoluble in isopropyl alcohol. What 'Iclaim and. desire to protect byLetters Patent is: I

'1. As a productyan aluminum dialkoxide'monoresinate selected from thegroup consisting of aluminum diisopropoxide monoresinate andaluminurndibutoxide monoresinate.

2.. .As. a product, aluminum diisopropoxide propoxide monoresinate whichcomprises reacting under anhydrous iconditionsaluminum triisopropoxideand rosin crystals in the proportion of -1 :mol of aluminumtriisopropoxide to 1 mol of res n crystals.

6. The method of producing alriminumdiisopropoxi'de 'monores'mate whichcomprises react- 8. The method of producing aluminum diisopropoxidemonoresinate which comprises react ing under anhydrous conditionsaluminum triisopropoxide and polymerized rosin in the ,proportion of 1mol of aluminum triisopropoxide to lmol of polymerizedrosin.

9. The method of producing aluminum diisopropoxide monoresinate whichcomprises reacting aluminum triisopropoxide and polymerized rosin in theproportion of 1 mo1 of aluminum triisopropoxide to 1 mol of polymerizedrosin in the presence of .an anhydrous solvent.

10. The method of producing aluminum diisopropoxide monoresinate whichcomprises reacting aluminum triisopropoxide and polymerized rosin in theproportion of 1. .mol of aluminum triisopropoxide to 1 mol ofpolymerized rosin in the presence of an anhydrous solvent, distillingoiT the alcohol set free, and recovering aluminum diisopropoxidemonoresinate from the solution.

ll/The method of producing aluminum :diisopropoxide monoresinate whichcomprises reacting under anhydrous conditions aluminum triisopropoxicleand hydrogenated rosin in the proportion of 1 mol of aluminumtriisopropoxide to 1 mol of hydrogenated rosin. j a

12. The method ofproducing aluminum; diisopropoxide monoresinate whichcomprises reacting aluminum triisopropoxide and hydrogenated rosin inthe proportion of 1 mol of aluminum triisopropoxide to 1 mol ofhydrogenated rosin in the presence of an anhydrous solvent.

13. The method of producing aluminum diisopropoxide monoresinate whichcomprises reacting aluminum triisopropoxide and hydrogenated rosin inthe proportion of 1 mol of aluminum 'triisopropoxide to 1 mol ofhydrogenated rosin in the presence of an anhydrous solvent, distillingoffthe alcohol set free, and recovering aluminumdiisopropoxidemonoresinate from the solution.

14. The method of producing an aluminum dialkoxide monoresinate whichvcomprises reacting under anhydrous conditions an aluminum -tri-' saidaluminum trialkoxide to lmol of'rosin. contacting thealuminum'dialkoxide monoresinate so formed with anhydrous butanol, andseparat ing said aluminum dialkoxide monoresin-atepin purified state asa residue insoluble in-Isaid huta nol. a 1 1 HAROLD M; SPURLIN'...

